[BH4-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)=[O:8].Cl>O.CCO>[OH:3][C:4]1[CH:5]=[C:6]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[OH:8])[CH:16]=[CH:17][CH:18]=1A solution of sodium borohydride (NaBH4) (0.19 g, 5.14 mmol) in H2O (5 mL) was added to an orange solution of 3,3′-dihydroxybenzophenone (1.00 g, 4.67 mmol) in EtOH (15 mL) and the resulting mixture was stirred for 1 h. After this time, the reaction mixture was added to ice-water (40 mL) containing conc. HCl (2.5 mL) and the solution was extracted with EtOAc (2×60 mL). The combined organic layers were washed with NaOH (3M, 2×50 mL) and the combined basic washes were acidified with conc. HCl. The organic components that appeared were extracted with EtOAc (2×100 mL). The combined EtOAc extracts were dried (MgSO4) and the solvent was removed in vacuo to give the crude product as a brown oil which solidified on standing. Purification was achieved by recrystallisation from H2O to give the title compound as a brown crystalline solid (0.86 g, 85%, mp 141-142° C.); δH (270 MHz, d6-DMSO) 9.27 (2H, br s, ArOH), 7.05 (2H, t, J=8.2, ArH), 6.84-6.72 (4H, m, ArH), 6.63-6.54 (2H, m, ArH), 5.72 (1H, br s, CHOH), 5.50 (1H, s, CHOH); δC (68 MHz, d6-DMSO) 157.1 (2×C), 147.2 (2×C), 128.9 (2×CH), 117.0 (2×CH), 113.6 (2×CH), 113.1 (2×CH), 74.1 (CH); LCMS (ES−) 215.0 ([M−H]−, 30%), 196.9 (10), 168.8 (15), 120.7 (100); HRMS (FAB+) Found 216.0785, C13H12O3 requires 216.0786.
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