4-(Benzyloxy)-3-(trifluoromethyl)benzoic acid → (4-Benzyloxy-3-trifluoromethylphenyl)methanol

HRID 901174Notes

Reaction equation

HRID 901174 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[C:18]([F:19])([F:21])[F:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 167490234-(Benzyloxy)-3-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 16749447(4-Benzyloxy-3-trifluoromethylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Benzyloxy-3-trifluoromethyl-benzoic acid (CAB03046, 3.555 g, 12 mmol) in THF (20 mL) was added dropwise to a suspension of lithium aluminium hydride (1.0 g, 26.3 mmol) in THF (20 mL). The mixture was stirred for another 30 minutes at room temperature and then quenched by addition of 2N NaOH (5 mL). The white preciptate was filtered off and washed with dichloromethane (100 mL), the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was crystallised from diethyl ether/hexane. Yield: 3.31 g (98%). 1H-NMR (400 MHz, CDCl3) δ=1.72 (t, J=5.9 Hz, 1H, —OH), 4.66 (d, J=5.9 Hz, 2H, —CH2OH), 5.21 (s, 2H, —CH2Ph), 7.02 (d, J=8.2 Hz, 1H), 7.30-7.48 (m, 6H), 7.61 (d, J=2.3 Hz, 1H). LRMS (FAB+): 91.1 (100), 265.2 (45), 282.2 (40, [M+H]+).

Workup

  1. customquenched by addition of 2N NaOH (5 mL)
  2. filtrationThe white preciptate was filtered off
  3. washwashed with dichloromethane (100 mL)
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil was crystallised from diethyl ether/hexane

Sources & evidence

ORD record
ord-1bcc1b55dde24c9592c8b4a7f674c240
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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