Benzyl Bromide → Methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate

HRID 389948Notes

Reaction equation

HRID 389948 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C>[CH2:22]([O:12][C:10]1[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59167875Methyl 2,4-dihydroxy-5-(propan-2-yl)benzoate

Product 1

HCID 58236452Methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (1.05 g, 5.0 mmol) and anhydrous potassium carbonate (828 mg, 6.0 mmol) in acetonitrile (25 ml) was treated with benzyl bromide (0.655 ml, 5.5 mmol) and the mixture was stirred at room temperature for 24 hours. The solvent was removed in vacuo and the residue was treated with water (50 ml). The solid material was collected by suction filtration, rinsed with water (2×50 ml) and sucked dry under reduced pressure to afford methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate (1.25 g, 83%) as colourless needles. 1H NMR (DMSO-d6) 10.68 (1H, br s), 7.57 (1H, s), 7.48-7.40 (4H, m), 7.34 (1H, m), 6.64 (1H, s), 5.20 (2H, s), 3.87 (3H, s), 3.18 (1H, m), 1.17 (6H, d). MS: [M+H]+ 301.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with water (50 ml)
  3. filtrationThe solid material was collected by suction filtration
  4. washrinsed with water (2×50 ml)
  5. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-cf283f84a5ec48deb85951e672327f21
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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