Methanol → HCID 12601891, compound

HRID 1993876Notes

Reaction equation

HRID 1993876 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:12](O)=[O:13])[C:6]([C:9](O)=[O:10])=[CH:7][CH:8]=1.B.CO>C1COCC1>[OH:13][CH2:12][C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:8]=[CH:7][C:6]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 5990394-(Trifluoromethyl)phthalic acid

Product 1

HCID 12601891HCID 12601891, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-trifluoromethylbenzene-1,2-dicarboxylic acid (5.85 g, 25 mmol) in THF (50 mL) at −78° C. was added borane in THF (1.0 M, 75 mL) and the mixture was stirred for 10 minutes. The mixture was then allowed to warm to room temperature and stirred overnight. Methanol (30 mL) was added and solvents were evaporated. The mixture was partitioned between ether and aqueous hydrochloric acid (1N). The organic layer was washed with brine and concentrated sodium bicarbonate solution. After the evaporation of solvents, colorless oil was obtained as (2-hydroxymethyl-4-trifluoromethyl-phenyl)-methanol (5.15 g). 1H-NMR (CDCl3) □ 7.58 (m, 2H), 7.51 (s 1H), 4.79 (s, 4H), 2.88 (m, 2H).

Workup

  1. stirringstirred overnight
  2. customsolvents were evaporated
  3. customThe mixture was partitioned between ether and aqueous hydrochloric acid (1N)
  4. washThe organic layer was washed with brine and concentrated sodium bicarbonate solution
  5. customAfter the evaporation of solvents

Sources & evidence

ORD record
ord-b30e4d2bcfa4482dba369db13e2bb663
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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